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2,3,5,6-Tetrafluorophenylhydrazine → 4-iodo-1-(2,3,5,6-tetrafluorophenyl)-1H-pyrazolo[3,4-b]pyridine

HRID 1186808
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1186808
F[C:2]1[N:9]=[CH:8][CH:7]=[C:6]([I:10])[C:3]=1[CH:4]=O.[F:11][C:12]1[C:17]([F:18])=[CH:16][C:15]([F:19])=[C:14]([F:20])[C:13]=1[NH:21][NH2:22]>CN1C(=O)CCC1>[I:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[N:21]([C:13]3[C:14]([F:20])=[C:15]([F:19])[CH:16]=[C:17]([F:18])[C:12]=3[F:11])[N:22]=[CH:4][C:3]=12
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 695522,3,5,6-TetrafluorophenylhydrazineHCID 99923282-Fluoro-4-iodopyridine-3-carbaldehyde

Produkt 1

HCID 866901794-iodo-1-(2,3,5,6-tetrafluorophenyl)-1H-pyrazolo[3,4-b]pyridineAusbeute 104,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
184 °C

Versuchsvorschrift

To a 15 mL pressure bottle was added 2-fluoro-4-iodonicotinaldehyde (710 mg, 2.83 mmol), (2,3,5,6-tetrafluorophenyl)hydrazine (509 mg, 2.83 mmol), and anhydrous NMP (4 mL). The reaction mixture was flushed with argon, securely capped, and heated at 184° C. for 2.75 h. The reaction mixture was partitioned with ethyl acetate (300 mL), water (125 mL), and brine (50 mL). The organic layer was washed with water (4×40 mL) and brine (75 mL) and the combined aqueous layers were extracted with additional ethyl acetate (300 mL). The second organic layer was washed with water (4×60 mL), and brine (100 mL), and the combined organic layers were dried over sodium sulfate, and evaporated in vacuo to give 1.16 g (quantitative yield) of the title compound as a tan solid. LC/MS (Condition B): ret. T=3.92 min, (M+H)+ 393.89.

Aufarbeitung

  1. customThe reaction mixture was flushed with argon
  2. customsecurely capped
  3. customThe reaction mixture was partitioned with ethyl acetate (300 mL), water (125 mL), and brine (50 mL)
  4. washThe organic layer was washed with water (4×40 mL) and brine (75 mL)
  5. extractionthe combined aqueous layers were extracted with additional ethyl acetate (300 mL)
  6. washThe second organic layer was washed with water (4×60 mL), and brine (100 mL)
  7. dry with materialthe combined organic layers were dried over sodium sulfate
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7f390854fa874cb584c6795bad2b217f
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673922B2

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